1,7-anhydro-2-deoxy-1-(hydroxymethyl)-3,4:5,6-di-O-isopropylidene-D-chiro-inositol | 415726-88-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,7-anhydro-2-deoxy-1-(hydroxymethyl)-3,4:5,6-di-O-isopropylidene-D-chiro-inositol
• 英文别名: (1S,2R,6R,7S,9R)-4,4,11,11-tetramethylspiro[3,5,10,12-tetraoxatricyclo[7.3.0.02,6]dodecane-7,2'-oxirane]
• CAS: 415726-88-4
• 化学式: C₁₃H₂₀O₅
• 分子量: 256.299
• InChiKey: JNDOHWOXZUWLSP-MGWGEXEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,7-anhydro-2-deoxy-1-(hydroxymethyl)-3,4:5,6-di-O-isopropylidene-D-chiro-inositol 在 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以92%的产率得到1-(azidomethyl)-2-deoxy-3,4:5,6-di-O-isopropylidene-D-chiro-inositol
  参考文献：
  名称：

  SYNTHESIS OF 1- AND 3-C-(AMINOMETHYL)-1,2,3,4,5-CYCLOHEXANEPENTOLS FROM (+)-epi-QUERCITOL1

  摘要：

  Oxidation of three di-O-isopropylidene derivatives 2a-4a, newly derived from (+)-epi-quercitol (1), with acetic anhydride in DMSO gave the corresponding ketones 5-7, which underwent aldol-type condensation with nitromethane under basic conditions to give selectively the protected derivatives 8a-10a of C-nitromethyl-1,2,3,4,5-cyclohexanepentols, respectively. On treatment with diazomethane in DMSO, the ketones 6 and 7 gave single spiro epoxides 11 and 12, the structures of which were confirmed by converting them into new C-(azidomethyl)cyclohexanepentols 16 and 17. The nitro compounds were hydrogenated in the presence of Raney nickel to give the amines isolated as the N-acetyl derivatives. Deprotection gave three new 1- and 3-C-aminomethyldeoxyinositols 15c-17c. The aminocyclitols obtained and their N-acetyl derivatives were assayed for inhibitory activity against examples of glycosidases.

  DOI：

  10.1081/car-100108284
• 作为产物：
  描述：

  2,3:4,5-di-O-isopropylidene-(+)-epi-quercitol 在 乙酸酐 、 二甲基亚砜 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 102.0h， 生成 1,7-anhydro-2-deoxy-1-(hydroxymethyl)-3,4:5,6-di-O-isopropylidene-D-chiro-inositol
  参考文献：
  名称：

  SYNTHESIS OF 1- AND 3-C-(AMINOMETHYL)-1,2,3,4,5-CYCLOHEXANEPENTOLS FROM (+)-epi-QUERCITOL1

  摘要：

  Oxidation of three di-O-isopropylidene derivatives 2a-4a, newly derived from (+)-epi-quercitol (1), with acetic anhydride in DMSO gave the corresponding ketones 5-7, which underwent aldol-type condensation with nitromethane under basic conditions to give selectively the protected derivatives 8a-10a of C-nitromethyl-1,2,3,4,5-cyclohexanepentols, respectively. On treatment with diazomethane in DMSO, the ketones 6 and 7 gave single spiro epoxides 11 and 12, the structures of which were confirmed by converting them into new C-(azidomethyl)cyclohexanepentols 16 and 17. The nitro compounds were hydrogenated in the presence of Raney nickel to give the amines isolated as the N-acetyl derivatives. Deprotection gave three new 1- and 3-C-aminomethyldeoxyinositols 15c-17c. The aminocyclitols obtained and their N-acetyl derivatives were assayed for inhibitory activity against examples of glycosidases.

  DOI：

  10.1081/car-100108284

文献信息

• SYNTHESIS OF 1- AND 3-C-(AMINOMETHYL)-1,2,3,4,5-CYCLOHEXANEPENTOLS FROM (+)-epi-QUERCITOL1
  作者：Seiichiro Ogawa、Hiroshi Aoyama、Yoji Tezuka

  DOI：10.1081/car-100108284

  日期：——

  Oxidation of three di-O-isopropylidene derivatives 2a-4a, newly derived from (+)-epi-quercitol (1), with acetic anhydride in DMSO gave the corresponding ketones 5-7, which underwent aldol-type condensation with nitromethane under basic conditions to give selectively the protected derivatives 8a-10a of C-nitromethyl-1,2,3,4,5-cyclohexanepentols, respectively. On treatment with diazomethane in DMSO, the ketones 6 and 7 gave single spiro epoxides 11 and 12, the structures of which were confirmed by converting them into new C-(azidomethyl)cyclohexanepentols 16 and 17. The nitro compounds were hydrogenated in the presence of Raney nickel to give the amines isolated as the N-acetyl derivatives. Deprotection gave three new 1- and 3-C-aminomethyldeoxyinositols 15c-17c. The aminocyclitols obtained and their N-acetyl derivatives were assayed for inhibitory activity against examples of glycosidases.